Cyanomethylphenethanolamines

Abstract

Preparation of cyanomethylphenethanolamines useful as adrenergic stimulants is described. Preferred compounds such as 2-hydroxy-5-[1-hydroxy-2-[(1,1-dimethyl-2-phenylethyl)amino]ethyl]-ben zeneacetonitrile are selective beta-adrenergic stimulants having relatively greater potency on respiratory smooth muscle than on cardiac muscle. Such compounds are particularly valuable in the treatment of bronchial conditions.

What is claimed is: 
     
       1. A compound selected from the group of phenethanolamines of the formula ##STR14##or a pharmaceutically acceptable acid addition salt thereof wherein R is hydrogen, methyl or ethyl;   R 1  is hydrogen or a radical selected from the group consisting of straight or branched chain lower alkyl of 1 to 6 carbon atoms inclusive, straight or branched chain lower alkyl of 1 to 6 carbon atoms substituted by phenyl, phenoxy, substituted phenyl or substituted phenoxy wherein said phenyl or phenoxy substituent is hydroxy, methoxy, or halogen.   
     
     
       2. The compound of claim 1 which is 2-hydroxy-5-[1-hydroxy-2-[(1,1-dimethyl-2-phenylethyl)amino]ethyl]benzeneacetonitrile. 
     
     
       3. The compound of claim 1 which is 2-hydroxy-5-[1-hydroxy-2-[(1,1-dimethyl-2-phenylethyl)amino]ethyl]benzeneacetonitrile hydrochloride. 
     
     
       4. A pharmaceutical composition in dosage unit form comprising a pharmaceutical carrier and an effective bronchodilating amount of a compound selected from the group of phenethanolamines of the formula ##STR15##or a pharmaceutically acceptable acid salt thereof wherein R is hydrogen, methyl or ethyl;   R 1  is hydrogen or a radical selected from the group consisting of straight or branched chain lower alkyl of 3 to 6 carbon atoms inclusive, straight or branched chain lower alkyl of 1 to 6 carbon atoms substituted by phenyl, phenoxy, substituted phenyl or substituted phenoxy wherein said phenyl or phenoxy substituent is hydroxy, methoxy, or halogen.   
     
     
       5. The pharmaceutical composition according to claim 4 in which the active ingredient is 2-hydroxy-5-[1-hydroxy-2-[(1,1-dimethyl-2-phenylethyl)amino]ethyl]benzeneacetonitrile. 
     
     
       6. The pharmaceutical composition according to claim 4 in which the active ingredient is 2-hydroxy-5-[1-hydroxy-2-[(1,1-dimethyl-2-phenylethyl)amino]ethyl]benzenacetonitrile hydrochloride. 
     
     
       7. A method for effecting bronchodilation in a mammal in need of such treatment which comprises administering to said mammal an effective bronchodilator amount of a compound selected from the group of phenethanolamines of the formula ##STR16##or a pharmaceutically acceptable acid addition salt thereof wherein R is hydrogen, methyl or ethyl;   R 1  is hydrogen or a radical selected from the group consisting of straight or branched chain lower alkyl of 3 to 6 carbon atoms inclusive, straight or branched chain lower alkyl of 1 to 6 carbon atoms substituted by phenyl, phenoxy, substituted phenyl or substituted phenoxy wherein said phenyl or phenoxy substituent is hydroxy, methoxy, or halogen.   
     
     
       8. The method of claim 7 wherein the effective amount ranges from 2 to 2000 mcg./kg. of body weight of said mammal. 
     
     
       9. The method of claim 7 wherein the compound is 2-hydroxy-5-[1-hydroxy-2-[(1,1-dimethyl-2-phenylethyl)amino]ethyl]benzeneacetonitrile. 
     
     
       10. The method of claim 7 wherein the compound is 2-hydroxy-5-[1-hydroxy-2-[(1,1-dimethyl-2-phenylethyl)amino]ethyl]benzeneacetonitrile hydrochloride.